Deals on vacations and trips to Smith Island

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Smith Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Lankford Hotel and Lodge

Lankford Hotel and Lodge

3.5 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $476, price is now $352 per person
$352
per person
Aug 15 - Aug 18
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A restaurant and a communal living room are also provided.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
Price was $1,129, price is now $774 per person
$774
per person
Aug 15 - Aug 18
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $823, price is now $595 per person
$595
per person
Aug 15 - Aug 18
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
This hotel features 4 restaurants, an outdoor pool, and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free WiFi.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $720, price is now $529 per person
$529
per person
Aug 15 - Aug 18
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
This aparthotel features a seasonal outdoor pool and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning and laundry facilities are also provided.
Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $693, price is now $511 per person
$511
per person
Aug 15 - Aug 18
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. Luggage storage is also provided.

Top Smith Island hotels deals

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island MD
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Ewell MD
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This cottage features laundry facilities.
Kitchen
Washer
Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Smith Island MD
$326 nightly
The price is $360 total per night
$360 total
Jul 15 - Jul 16
Total with taxes and fees
A gym is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK & golf cart rental

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK & golf cart rental

Smith Island MD
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

Smith Island MD
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

2 out of 5
700 Norris Harbor Dr Crisfield MD
Free Cancellation
$110 nightly
The price is $125 total per night
$125 total
Jul 27 - Jul 28
Total with taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this motel. WiFi in public areas is free. A garden and a picnic area are also provided.
Pool
Pet friendly
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Smith Island attractions

Smith Island

9.0/10 (21 reviews)
Commune with nature and explore the great outdoors at Smith Island during your travels in Smith Island. Discover the sunsets in this relaxing area, or seek out the fishing spots.
See properties

Frequently asked questions

How much are vacation packages to Smith Island?
With vacation packages being sold for only $352, you won't need to blow out the credit card for your getaway to Smith Island. Travelocity is here to help. Bundle flights, hotels and tours into a convenient package and land some fantastic discounts. The more you book, the greater the savings.
Where can I get the best vacation package deals for Smith Island?
You'll discover a tempting selection of Smith Island package deals on Travelocity. With 400 partner airlines and 1,000,000 properties across the globe, putting together your ultimate escape will be a piece of cake.
Why should I book my Smith Island vacation bundle via Travelocity?
The three S's — savings, support and a stress-free booking — are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you can rely on round-the-clock support. With the Travelocity Price Match Guarantee, you can relax knowing you'll always get the best deal available.
Can I save on my Smith Island car rental if I combine it with my hotel or flight?
With a Smith Island vacation package, you can bundle your car, hotel and flight bookings and save a ton. If you want to see the best of this fabulous region, why not make tracks to White House? This well-known sight is 85 mi from Smith Island. With your own set of wheels, you'll be there before you know it.
Which airport is best for Smith Island?
Salisbury - Ocean City Wicomico Regional Airport (SBY), the gateway to Smith Island, is where you'll get off the plane. You'll find it 35 mi northeast of the center of town.
Where should I stay when visiting Smith Island?
If you're after a place to base yourself, check out the Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage. It's the top pick for many visitors.

Photos of local treasures

Browse Smith Island vacation photos for more inspiration

A person in a kayak on a calm body of water during sunset.